The Digital Contrarian

TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind Takeaways

• Ryan Levesque • Episode 65

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TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind Takeaways

Episode Summary

In this episode of The Digital Contrarian, host Ryan Levesque dives into the $1.5 billion Anthropic settlement and its implications for content creators.

You'll learn why we may be exiting the "Napster era" of AI, discover the contrarian content strategy behind our first viral YouTube video, and explore 27 transformative insights from the Vermont Farm Mastermind Experience.

Question of the Day 🗣️

What's your biggest takeaway from the 27 Vermont insights? Which one could transform your business?

Key Take-aways

  • The $1.5 billion Anthropic settlement signals a shift from the "Napster era" to the "Spotify era" of AI
  • YouTube may be the next AI battleground as the last non-AI powered search engine
  • Single source of truth content can generate viral breakthrough results (27K+ views in 18 weeks)
  • Strategic content ecosystems outperform shallow algorithm gaming every time
  • Vermont Farm Mastermind revealed 27 transformative business and life insights

Timestamped Outline ⏱️

00:00 – The AI battle brewing beneath the surface
00:48 – $1.5 billion Anthropic settlement breakdown
02:15 – From Napster era to Spotify era of AI
03:40 – YouTube as the next AI battleground
04:30 – Town Hall announcement: October 2nd
05:35 – Unexpected YouTube breakthrough explained
06:35 – Vermont Farm Mastermind experience
07:25 – 27 takeaways from Maeve Ferguson's perspective

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Credits

Host: Ryan Levesque
© 2025 RL & Associates LLC. All rights reserved.

The AI battle brewing beneath the surface and 27 other takeaways from my Vermont Farm Mastermind experience. On the eve of my Vermont Mastermind experience last week, the AI company Anthropic agreed to pay a record $1.5 billion settlement to resolve a copyright lawsuit over the illegal downloading of over 500,000 books to train its Claude.ai chatbot. Now, this is a big deal, and here's why. 

First, this is the largest payout ever in the history of US copyright cases, which is massive in and of itself. But second, this is the first ever class action settlement in the United States involving AI and copyright, which is huge. Because with more than 40 other active copyright lawsuits versus AI companies currently underway, now with more likely coming, this may represent a turning point in the so-called dog and cat battle between content creators and AI companies. 

Now, the question, of course, is how should we be thinking about this twist? Well, as it was described in a private group that I'm part of, this may be a signal that we're exiting the so-called Napster era of AI and entering into the Spotify era of AI. And if that's the case, well, it's likely that future payouts may be measured in nickels and dimes with the $1.5 billion lawsuit, Anthropic will be paying roughly $3,000 per work to over 500,000 authors around the world. Now, in the course of human history, building empires on the backs of unpaid labor is, of course, nothing new. 

And in this latest variation, if book authors were the first victims of the great AI content heist, it looks like video creators may be next. In fact, according to a breakthrough investigation by the Atlantic, at least 15 million YouTube videos and counting have been scraped without permission by AI companies to train their data sets, explicitly violating the platform's terms of service. By the way, you can see if any of your YouTube videos have been included in these data sets by searching the data sets on the link provided by the Atlantic, which we'll make sure to link to in the description. 

So does this mean we should be running away from YouTube? Well, I actually think it means the exact opposite, because as arguably the last remaining non-AI powered search engine online, I think YouTube may be the next big AI battleground. I mean, watch this space. In fact, speaking of YouTube, my upcoming town hall and an unexpected YouTube breakthrough. 

After receiving an overwhelming expression of interest, I've decided that I am going to host the town hall that I mentioned in last week's episode of the Digital Contrarian. Thank you, by the way, to everyone who took the time to leave a comment and write in. But with all my commitments on my plate this fall, coaching soccer, farm harvest, finishing my forthcoming book, serving as a private advisor to my advisory clients, not to mention traveling, speaking events, et cetera, et cetera, et cetera. 

I've had to thread the needle with my schedule. Now, the good news is that I've been able to find a time and date that I can make work for this town hall event. So I invite you to save the date.

The date is Thursday, October 2nd at 11 a.m. U.S. Central Time, which is 12 o'clock U.S. Eastern Time. This is a live town hall event with yours truly, Ryan Levesque, and I plan on blocking off 90 minutes for the event. I'll be following up in the coming weeks with a Zoom registration link and details. 

But in the meantime, I just wanted to give you a quick note. Similar to past town hall events like this, the live Zoom meeting will be capped at 300 attendees and will very likely fill up beyond capacity. So if you're interested in joining me for this session, be sure to keep your eyes peeled for registration details. 

There's no cost to attend, but it is first come, first serve. Now, one of the things that I'll be talking about in this town hall is what we've learned in the last six months building from scratch the strategic content ecosystem that I wrote about most recently in July of 2025 in issue number 55 of the Digital Contrarian, my contrarian YouTube strategy. We'll make sure to provide a link in the description to that issue of the newsletter.

For example, barely 18 weeks into executing the YouTube portion of the strategy, we've already had our first long form video pop over 27,000 views and counting at the time of this video, and that number is likely to go up. Now, I thought it would take us at least a year to see a video pop like this, because to be clear, this is not some shallow attention chasing video or an attempt to try to game the algorithm. Instead, this 14 minute video is filled with original thought leadership, and it is very much intended to cultivate influence, as I wrote about back in issue number 31 of the Digital Contrarian, cultivating influence versus chasing attention.

But more importantly, this video is an example of the return to real principles in action. And it's an example of what can happen when you take a single source of truth piece of content, i.e. like a weekly newsletter that you personally write yourself along the lines of the Digital Contrarian and then strategically repurpose it for discovery in a dozen different places across the internet, including long form video on YouTube. So why did this video pop? Well, I'll walk you through exactly what we're doing as well as why I think this video popped along with some of the biggest lessons that we've learned in this process, all on this upcoming town hall event, which takes us to 27 other takeaways from my Vermont mastermind. 

Originally, in this issue of the Digital Contrarian, I was planning on summarizing some of my biggest takeaways from our most recent Vermont farm mastermind experience. But one of the founders, one of the entrepreneurs in attendance, Maeve Ferguson, who's pictured in the foreground in this photo, wrote an excellent piece this week, sharing some of her biggest takeaways. Things like what are the non-obvious questions to be asking when you're stuck, how to rethink about the actual moat that's really protecting your business, and why studying anthropology is so important in this age of AI, and much, much more.

And I thought it would be cool for you to be able to read about the experience through the eyes of someone other than myself who was actually in the room. I'll share some of my own biggest insights in a future episode. So without further delay, I'm going to wrap today's issue by sharing a link to the article that Maeve published this weekend, which I highly recommend checking out, and which you can access in the description. 

It's titled, 27 Takeaways from Ryan Levesque's Vermont Mastermind Experience. I'm curious, by the way, when you have a chance to check it out, which of these 27 is your biggest takeaway. Okay, I'll leave you with that for now. 

Have a great rest of your week. Remember to hug the ones you love, as always. And until next week, I wish you all my best. 

Take care, and we'll talk soon.